Oakland Vacations from $178

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Your Oakland Vacation

From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.

The Latest Oakland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG
Hilton Garden Inn Pittsburgh Airport
Americas Best Value Inn Pittsburgh Airport
Fairmont Pittsburgh
DoubleTree by Hilton Pittsburgh - Green Tree

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland

Oakland Hotel Deals

Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $136 total per night from Nov 3 to Nov 4
$136 total
Nov 3 - Nov 4
Total with taxes and fees
8.8/10 Excellent! (482 reviews)
Rom was good but my 2 sons and I had breakfast that had cold toast and just warm sausage and eggs. My sons that had burritos were presented ok

Reviewed on Oct 27, 2025

Courtyard by Marriott Pittsburgh University Center
Hotel Indigo Pittsburgh University-Oakland by IHG

Hotel Indigo Pittsburgh University-Oakland by IHG

3.5 out of 5
329 Technology Drive, Pittsburgh, PA
Fully refundable
$111 nightly
The price is $127 total per night from Nov 23 to Nov 24
$127 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
Clean nicely decorated, and the shuttle service was a plus

Reviewed on Oct 16, 2025

Hotel Indigo Pittsburgh University-Oakland by IHG
The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
5130 Bigelow Boulevard, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $214 total per night from Nov 23 to Nov 24
$214 total
Nov 23 - Nov 24
Total with taxes and fees
9.2/10 Wonderful! (698 reviews)
Clean room. Friendly staff. Great room service. Able to honor disability accommodation. Very helpful.

Reviewed on Oct 20, 2025

The Oaklander Hotel, Autograph Collection
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Things to do

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.